A white church with a steeple and red accents, surrounded by autumn trees.

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Windham bed & breakfast

A garden with a stone wall, various plants, and flowers.

1. Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (148 reviews)
"Breakfast was wonderful!"
United States
Karen
$238 nightly
The price is $260
Oct 25 - Oct 26
Total with taxes and fees
Fleetwood House Bed & Breakfast
A multi-story building with a stone facade, multiple windows, and awnings.

2. Inn at St John Portland In-Town

Inn at St John Portland In-Town
2.5 star property
Valley Street
8.6 out of 10, Excellent, (1,170 reviews)
"Great location . Staff was awesome"
United States
Shad
$98 nightly
The price is $107
Nov 3 - Nov 4
Total with taxes and fees
Inn at St John Portland In-Town
A large brick house with a well-maintained garden, a front door, and a visible mailbox.

3. Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.
3.5 star property
West End
9.6 out of 10, Exceptional, (200 reviews)
"Place was charming and quirky. Very comfortable and well located."
United States
Mary
$244 nightly
The price is $266
Nov 17 - Nov 18
Total with taxes and fees
Blind Tiger Portland - Danforth Street.
A well-lit living room with a fireplace, comfortable seating, and a large mirror.

4. Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street
3.5 star property
West End
9.6 out of 10, Exceptional, (137 reviews)
"Beautiful place"
United States
Samuel
$207 nightly
The price is $226
Nov 17 - Nov 18
Total with taxes and fees
Blind Tiger Portland – Carleton Street
Exterior

5. West End Collection at 146 Pine

West End Collection at 146 Pine
3.0 star property
West End
9.6 out of 10, Exceptional, (100 reviews)
"This was a super cute boutique inn and the location was ideal. The staff was super friendly!"
United States
Stephanie
$212 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
West End Collection at 146 Pine
An outdoor deck with a stone fireplace, a sofa with American flag cushions, and a wicker chair.

6. The Perkins House

The Perkins House
3.0 star property
Cornish
9.8 out of 10, Exceptional, (131 reviews)
"Nice rooms and decorations, easy parking"
United States
Lan
$127 nightly
The price is $139
Nov 13 - Nov 14
Total with taxes and fees
The Perkins House
A black front door with a light fixture above it, flanked by two potted evergreen trees.

7. The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe
3.0 star property
Freeport
9.6 out of 10, Exceptional, (184 reviews)
"Great place"
United States
Mark
$203 nightly
The price is $221
Nov 1 - Nov 2
Total with taxes and fees
The Orchard House: Inn & Cafe
A porch with white wicker chairs and a red cushion, a wooden deck, and a sign for the Noble House Inn in the background.

8. Noble House Inn

Noble House Inn
3.5 star property
Bridgton
9.6 out of 10, Exceptional, (134 reviews)
"All the staff, and even the lodgers were extremely nice. Very clean, cozy, and pleasant stay. I will make sure all my friends and family lodge at the Noble House after my move."
United States
Michael
$125 nightly
The price is $136
Nov 23 - Nov 24
Total with taxes and fees
Noble House Inn
A covered porch with white railings and a view of a well-maintained lawn and pathway.

9. The Kendall Inn

The Kendall Inn
3.5 star property
Freeport
9.8 out of 10, Exceptional, (166 reviews)
"The breakfasts were so tasty! The Inn is so charming! We loved our stay and hope to return next year!"
United States
Justin Terry
$176 nightly
The price is $192
Nov 24 - Nov 25
Total with taxes and fees
The Kendall Inn
A white building with a red roof, a sign indicating a vacancy at Candlebay Inn, and an American flag.

10. Candlebay Inn

Candlebay Inn
3.0 star property
Freeport
9.6 out of 10, Exceptional, (497 reviews)
"Great stay in a historic home."
United States
Richard
$143 nightly
The price is $156
Nov 3 - Nov 4
Total with taxes and fees
Candlebay Inn
A covered patio with wicker furniture and a mosaic table, surrounded by greenery and a white building.

11. Old Orchard Beach Inn

Old Orchard Beach Inn
2.5 star property
Old Orchard Beach
8.2 out of 10, Very good, (1,002 reviews)
"Really nice hotel"
United States
James
$136 nightly
The price is $148
Nov 9 - Nov 10
Total with taxes and fees
Old Orchard Beach Inn
A brick building with a white entrance, steps leading up to a door, and potted plants on either side.

12. The Jeremiah Mason House B & B

The Jeremiah Mason House B & B
3.0 star property
Limerick
9.6 out of 10, Exceptional, (66 reviews)
"Beautiful Bed & Breakfast. Owner was great!! Super breakfast!!"
United States
Michael
$163 nightly
The price is $177
Oct 26 - Oct 27
Total with taxes and fees
The Jeremiah Mason House B & B
A two-story house with a balcony, a front porch, and a snow-covered landscape.

13. The Nicholson Inn

The Nicholson Inn
3.0 star property
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"We had a fantastic and lovely, although quick, stay. The Inn is very charming and John and Loretta are so kind and helpful. Would love to go back and stay with them again.."
United States
alexandre
$246 nightly
The price is $268
Nov 16 - Nov 17
Total with taxes and fees
The Nicholson Inn
A house with a sign for The James Place Inn, indicating a vacancy.

14. The James Place Inn B&B

The James Place Inn B&B
3.5 star property
Freeport
10.0 out of 10, Exceptional, (196 reviews)
"Sean was amazingly helpful and friendly. The house itself is so well maintained, and the blue room was adorable. Loved the fact that we were within walking distance of all the shops. Would definitely recommend and will plan on staying again the next time we’re in town."
United States
Kim
$251 nightly
The price is $273
Nov 9 - Nov 10
Total with taxes and fees
The James Place Inn B&B
A long dining table set for a meal with multiple chairs, candles, and decorative centerpieces.

15. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
10.0 out of 10, Exceptional, (1 review)
"Really cool home and room was big and clean!"
United States
Daniel
$199 nightly
The price is $217
Nov 1 - Nov 2
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
A two-story house with a snow-covered roof and a porch.

16. The Munroe Inn

The Munroe Inn
3.5 star property
Auburn
9.2 out of 10, Wonderful, (78 reviews)
"Wonderful place to stay. The rooms are so comfortable and the host was very accommodating. Breakfast was outstanding and the best cup of coffee in Auburn. Such a gem of a place!"
United States
Tristan
$178 nightly
The price is $194
Nov 17 - Nov 18
Total with taxes and fees
The Munroe Inn
A spacious kitchen with a large wooden table, a built-in stove, and a fireplace.

17. The Diamond Island Suite - Suite in Historic Home

The Diamond Island Suite - Suite in Historic Home
West End
$253 nightly
The price is $276
Nov 1 - Nov 2
Total with taxes and fees
The Diamond Island Suite - Suite in Historic Home
A long dining table set for a meal with multiple chairs, candles, and decorative centerpieces.

18. Experience the History of Portland - The Hope Island Room

Experience the History of Portland - The Hope Island Room
West End
$270 nightly
The price is $294
Nov 1 - Nov 2
Total with taxes and fees
Experience the History of Portland - The Hope Island Room
A staircase with a wooden handrail and black steps, leading to a room with patterned wallpaper and a chandelier.

19. Experience the History of Portland - Two Room Suite w/Private Bath

Experience the History of Portland - Two Room Suite w/Private Bath
West End
$361 nightly
The price is $393
Nov 1 - Nov 2
Total with taxes and fees
Experience the History of Portland - Two Room Suite w/Private Bath
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

20. The Loft - private suite in historic home

The Loft - private suite in historic home
West End
$445 nightly
The price is $485
Nov 8 - Nov 9
Total with taxes and fees
The Loft - private suite in historic home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"The room was clean. I did not care for the view of the graffiti or trash bins outside our low level room. The hotel rooms need to be cleaned and update"
Elisabeth 1-night trip
Posted less than an hour ago
Portland Regency Hotel & Spa

Find out more about Windham

Windham B&B information

Number of reviews
1,346
Accommodation
41 B&B
Lowest Price
$107
Highest Price
$485

Frequently asked questions

What is the nightly rate for a B&B in Windham?
Prices for B&Bs in Windham often vary, but you can find a great deal from $107 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Windham?
The best time to book a B&B in Windham is during the vibrant fall season, particularly from September to October. This period is favored by travelers seeking a picturesque escape amid the stunning autumn foliage. As the leaves change, Windham transforms into a canvas of brilliant reds, oranges, and yellows, providing a breathtaking backdrop for outdoor activities and leisurely strolls.

September offers mild temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, making it ideal for hiking and exploring the scenic trails in the Catskill Mountains. The comfortable climate invites visitors to engage in outdoor adventures, whether it's a hike to the summit of Windham Mountain or a bike ride through the charming countryside.

If you are considering a more budget-friendly option, late October can be particularly appealing. This month often features fewer crowds, allowing for a peaceful retreat where you can enjoy the lingering fall beauty without the hustle and bustle. Plus, many local businesses offer seasonal promotions, giving you the opportunity to enjoy quality experiences at a great value.
What is the difference between a Windham Bed & Breakfast and a hotel?
Every Windham B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windham B&Bs.

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